NPASS Compound

Structure

CID290529 OpenBabel06191716102D 39 45 0 0 1 0 0 0 0 0999 V2000 5.6356 -0.6760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4270 -1.6838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -2.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 -1.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1351 -6.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9823 -5.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1998 0.1155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1302 -0.1868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2879 -5.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2694 -0.1868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9823 -4.5807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3960 -4.1295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1998 -3.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9588 -3.0324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7052 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6356 -2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5609 -3.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2879 -4.5807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1302 -2.7480 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6944 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1351 -4.0916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0506 -3.4025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2694 -2.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7052 -1.9565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8472 -2.4457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6356 -3.2371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7052 -3.5394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 -0.4891 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4214 -2.6111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6944 -1.9565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9317 -3.1347 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0235 -3.5048 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1194 -4.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4270 -3.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4029 -4.4698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3783 -2.4077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 15 1 0 0 0 0 9 19 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 18 1 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 14 33 1 0 0 0 0 15 1 1 6 0 0 0 15 25 1 0 0 0 0 16 27 2 0 0 0 0 17 26 1 0 0 0 0 17 31 1 6 0 0 0 18 19 1 0 0 0 0 19 22 1 0 0 0 0 20 13 1 6 0 0 0 20 25 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 21 32 1 6 0 0 0 22 33 1 0 0 0 0 23 12 1 1 0 0 0 23 26 1 0 0 0 0 23 34 1 0 0 0 0 24 35 2 0 0 0 0 25 16 1 1 0 0 0 26 32 1 6 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 37 2 0 0 0 0 29 31 1 6 0 0 0 29 39 1 0 0 0 0 30 32 1 0 0 0 0 30 34 2 0 0 0 0 30 38 1 0 0 0 0 31 4 1 6 0 0 0 31 39 1 0 0 0 0 32 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.26
Volume:	544.349
LogP:	3.83
LogD:	3.798
LogS:	-4.578
# Rotatable Bonds:	2
TPSA:	108.63
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	6.2
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847
MDCK Permeability:	1.4543364159180783e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.084
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.221

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.422
Plasma Protein Binding (PPB):	97.42298126220703%
Volume Distribution (VD):	0.346
Pgp-substrate:	3.3465285301208496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.716
CYP2C19-inhibitor:	0.597
CYP2C19-substrate:	0.754
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.483
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.473

ADMET: Excretion

Clearance (CL):	7.55
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.184
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.242
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.281
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.966

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC290529

Natural Product ID:	NPC290529
*Common Name:**	Chaetoglobosin U
IUPAC Name:	n.a.
Synonyms:	Chaetoglobosin U
Standard InCHIKey:	MRENMDHAGXAXRK-QFHPAQOTSA-N
Standard InCHI:	InChI=1S/C32H36N2O5/c1-15-8-7-10-21-29-31(4,39-29)17(3)26-23(12-18-14-33-22-11-6-5-9-19(18)22)34-30(38)32(21,26)24(35)13-20-25(15)16(2)27(36)28(20)37/h5-7,9-11,14-15,17,20-21,23,25-26,29,33,36H,8,12-13H2,1-4H3,(H,34,38)/b10-7+/t15-,17-,20+,21-,23-,25-,26-,29-,31+,32+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@H]2[C@@H]3O[C@]3(C)[C@H]([C@@H]3[C@@]2(C(=O)C[C@@H]2[C@@H]1C(=C(C2=O)O)C)C(=N[C@H]3Cc1c[nH]c2c1cccc2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448756
PubChem CID:	11570022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans [CHEMONTID:0003767] Chaetoglobosins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12357398]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12483566]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497948]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921417]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209910]
NPO32736	chaetomium globosum ifb-e019	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499339]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872138]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16904330]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125234]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17827664]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	Ginkgo biloba	n.a.	n.a.	PMID[19246197]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19427327]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20225834]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20814854]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	isolated from the leaves of Viguiera robusta	n.a.	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21548578]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21640594]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854043]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22112725]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22593034]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23072467]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	Xichang of Sichuan Province, China	n.a.	PMID[26125976]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26343828]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5066072]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7116505]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]
NPO24171	Chaetomium globosum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	16000.0	nM	PMID[565110]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC290529 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	1584
0.2-0.3	5460
0.3-0.4	19780
0.4-0.5	11165
0.5-0.6	2455
0.6-0.7	1712
0.7-0.8	164
0.8-0.85	11
0.85-0.9	7
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC267926
0.942	High Similarity	NPC266192
0.942	High Similarity	NPC147446
0.9378	High Similarity	NPC57690
0.9009	High Similarity	NPC141428
0.89	High Similarity	NPC203614
0.8744	High Similarity	NPC235885
0.872	High Similarity	NPC204491
0.8667	High Similarity	NPC87856
0.8632	High Similarity	NPC132211
0.8552	High Similarity	NPC70155
0.8538	High Similarity	NPC267965
0.8519	High Similarity	NPC2395
0.8491	Intermediate Similarity	NPC151976
0.8476	Intermediate Similarity	NPC258062
0.8429	Intermediate Similarity	NPC225821
0.8349	Intermediate Similarity	NPC271862
0.8302	Intermediate Similarity	NPC127677
0.8301	Intermediate Similarity	NPC11445
0.8286	Intermediate Similarity	NPC98715
0.8255	Intermediate Similarity	NPC46225
0.8252	Intermediate Similarity	NPC195239
0.8252	Intermediate Similarity	NPC157828
0.7909	Intermediate Similarity	NPC474412
0.785	Intermediate Similarity	NPC300183
0.7721	Intermediate Similarity	NPC252338
0.7706	Intermediate Similarity	NPC18661
0.7675	Intermediate Similarity	NPC476818
0.7668	Intermediate Similarity	NPC471284
0.7661	Intermediate Similarity	NPC477043
0.7658	Intermediate Similarity	NPC235900
0.7656	Intermediate Similarity	NPC99428
0.765	Intermediate Similarity	NPC260900
0.7642	Intermediate Similarity	NPC472762
0.7642	Intermediate Similarity	NPC47190
0.76	Intermediate Similarity	NPC96131
0.7585	Intermediate Similarity	NPC300688
0.7581	Intermediate Similarity	NPC227582
0.7569	Intermediate Similarity	NPC476874
0.7546	Intermediate Similarity	NPC477044
0.7546	Intermediate Similarity	NPC477041
0.7545	Intermediate Similarity	NPC229348
0.7536	Intermediate Similarity	NPC213468
0.7523	Intermediate Similarity	NPC267343
0.7512	Intermediate Similarity	NPC74413
0.75	Intermediate Similarity	NPC475778
0.7489	Intermediate Similarity	NPC123019
0.7489	Intermediate Similarity	NPC234999
0.7488	Intermediate Similarity	NPC151939
0.7431	Intermediate Similarity	NPC477045
0.7424	Intermediate Similarity	NPC61813
0.7383	Intermediate Similarity	NPC154339
0.7381	Intermediate Similarity	NPC71037
0.7366	Intermediate Similarity	NPC201700
0.7336	Intermediate Similarity	NPC476516
0.733	Intermediate Similarity	NPC476073
0.7324	Intermediate Similarity	NPC235684
0.7324	Intermediate Similarity	NPC315555
0.7306	Intermediate Similarity	NPC131887
0.7304	Intermediate Similarity	NPC311276
0.7294	Intermediate Similarity	NPC231342
0.7289	Intermediate Similarity	NPC478158
0.7269	Intermediate Similarity	NPC35208
0.7261	Intermediate Similarity	NPC281049
0.7252	Intermediate Similarity	NPC193761
0.7252	Intermediate Similarity	NPC155143
0.724	Intermediate Similarity	NPC79129
0.724	Intermediate Similarity	NPC313985
0.724	Intermediate Similarity	NPC81654
0.724	Intermediate Similarity	NPC49196
0.724	Intermediate Similarity	NPC249150
0.724	Intermediate Similarity	NPC195461
0.7237	Intermediate Similarity	NPC472291
0.7227	Intermediate Similarity	NPC149708
0.7222	Intermediate Similarity	NPC95783
0.722	Intermediate Similarity	NPC253482
0.7217	Intermediate Similarity	NPC302191
0.7215	Intermediate Similarity	NPC282033
0.7212	Intermediate Similarity	NPC162860
0.7207	Intermediate Similarity	NPC475506
0.7205	Intermediate Similarity	NPC478157
0.7205	Intermediate Similarity	NPC313640
0.7204	Intermediate Similarity	NPC55772
0.7196	Intermediate Similarity	NPC163421
0.7196	Intermediate Similarity	NPC188387
0.7191	Intermediate Similarity	NPC79107
0.7191	Intermediate Similarity	NPC475424
0.7183	Intermediate Similarity	NPC469358
0.7177	Intermediate Similarity	NPC314603
0.7174	Intermediate Similarity	NPC251936
0.715	Intermediate Similarity	NPC160105
0.715	Intermediate Similarity	NPC165201
0.7149	Intermediate Similarity	NPC50503
0.7149	Intermediate Similarity	NPC67288
0.7143	Intermediate Similarity	NPC249428
0.7143	Intermediate Similarity	NPC206967
0.7143	Intermediate Similarity	NPC477135
0.7137	Intermediate Similarity	NPC469743
0.7137	Intermediate Similarity	NPC223791
0.7137	Intermediate Similarity	NPC107077
0.7131	Intermediate Similarity	NPC475648
0.713	Intermediate Similarity	NPC119700
0.7125	Intermediate Similarity	NPC475426
0.7124	Intermediate Similarity	NPC54420
0.7119	Intermediate Similarity	NPC24370
0.7119	Intermediate Similarity	NPC319232
0.7118	Intermediate Similarity	NPC219087
0.7116	Intermediate Similarity	NPC280290
0.7112	Intermediate Similarity	NPC477714
0.7109	Intermediate Similarity	NPC267885
0.7105	Intermediate Similarity	NPC475165
0.7098	Intermediate Similarity	NPC474116
0.7097	Intermediate Similarity	NPC321708
0.7095	Intermediate Similarity	NPC97525
0.709	Intermediate Similarity	NPC94541
0.709	Intermediate Similarity	NPC470843
0.7089	Intermediate Similarity	NPC14116
0.7089	Intermediate Similarity	NPC285411
0.7089	Intermediate Similarity	NPC198339
0.7085	Intermediate Similarity	NPC214428
0.7083	Intermediate Similarity	NPC323752
0.7078	Intermediate Similarity	NPC67551
0.7075	Intermediate Similarity	NPC111275
0.7074	Intermediate Similarity	NPC250129
0.7072	Intermediate Similarity	NPC473640
0.7067	Intermediate Similarity	NPC474561
0.7067	Intermediate Similarity	NPC49954
0.7062	Intermediate Similarity	NPC203468
0.7062	Intermediate Similarity	NPC110500
0.7062	Intermediate Similarity	NPC149155
0.7061	Intermediate Similarity	NPC284102
0.7059	Intermediate Similarity	NPC134384
0.7059	Intermediate Similarity	NPC311196
0.7053	Intermediate Similarity	NPC40779
0.7042	Intermediate Similarity	NPC283219
0.7042	Intermediate Similarity	NPC126709
0.7042	Intermediate Similarity	NPC248041
0.704	Intermediate Similarity	NPC100321
0.704	Intermediate Similarity	NPC293917
0.7039	Intermediate Similarity	NPC473310
0.7039	Intermediate Similarity	NPC264285
0.7033	Intermediate Similarity	NPC78020
0.7033	Intermediate Similarity	NPC476517
0.7026	Intermediate Similarity	NPC30570
0.7024	Intermediate Similarity	NPC469762
0.7022	Intermediate Similarity	NPC162730
0.7021	Intermediate Similarity	NPC471506
0.7018	Intermediate Similarity	NPC34271
0.7018	Intermediate Similarity	NPC213629
0.7017	Intermediate Similarity	NPC475601
0.7017	Intermediate Similarity	NPC476491
0.7017	Intermediate Similarity	NPC146824
0.7017	Intermediate Similarity	NPC475258
0.7014	Intermediate Similarity	NPC181502
0.7014	Intermediate Similarity	NPC85066
0.7013	Intermediate Similarity	NPC473547
0.7013	Intermediate Similarity	NPC475602
0.7013	Intermediate Similarity	NPC54744
0.7012	Intermediate Similarity	NPC238278
0.701	Intermediate Similarity	NPC211572
0.701	Intermediate Similarity	NPC80597
0.701	Intermediate Similarity	NPC75540
0.701	Intermediate Similarity	NPC70922
0.701	Intermediate Similarity	NPC212376
0.7009	Intermediate Similarity	NPC470279
0.7009	Intermediate Similarity	NPC470497
0.7005	Intermediate Similarity	NPC94752
0.7	Intermediate Similarity	NPC150698
0.7	Intermediate Similarity	NPC473689
0.7	Intermediate Similarity	NPC292416
0.7	Intermediate Similarity	NPC320968
0.7	Intermediate Similarity	NPC96801
0.6996	Remote Similarity	NPC477715
0.6996	Remote Similarity	NPC171317
0.6992	Remote Similarity	NPC16352
0.6987	Remote Similarity	NPC475362
0.6983	Remote Similarity	NPC97388
0.6979	Remote Similarity	NPC276657
0.6976	Remote Similarity	NPC469785
0.6975	Remote Similarity	NPC909
0.6975	Remote Similarity	NPC475338
0.6974	Remote Similarity	NPC88008
0.6971	Remote Similarity	NPC319880
0.6971	Remote Similarity	NPC244839
0.6971	Remote Similarity	NPC63031
0.6971	Remote Similarity	NPC213143
0.6971	Remote Similarity	NPC320324
0.6971	Remote Similarity	NPC469748
0.697	Remote Similarity	NPC75634
0.6966	Remote Similarity	NPC82070
0.6964	Remote Similarity	NPC78609
0.6963	Remote Similarity	NPC6093
0.6962	Remote Similarity	NPC64216
0.6962	Remote Similarity	NPC76565
0.6961	Remote Similarity	NPC259644
0.6961	Remote Similarity	NPC469763
0.6961	Remote Similarity	NPC25008
0.6961	Remote Similarity	NPC73952
0.6961	Remote Similarity	NPC469786
0.6961	Remote Similarity	NPC469765

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC290529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	534
0.2-0.3	672
0.3-0.4	2262
0.4-0.5	3101
0.5-0.6	1874
0.6-0.7	473
0.7-0.8	20
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7466	Intermediate Similarity	NPD7957	Phase 1
0.7466	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD2091	Phase 2
0.7393	Intermediate Similarity	NPD2096	Phase 2
0.7346	Intermediate Similarity	NPD2092	Phase 2
0.7346	Intermediate Similarity	NPD2094	Phase 2
0.7346	Intermediate Similarity	NPD2095	Phase 2
0.7342	Intermediate Similarity	NPD5426	Phase 3
0.7281	Intermediate Similarity	NPD7707	Approved
0.7281	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD4600	Approved
0.724	Intermediate Similarity	NPD4601	Approved
0.7143	Intermediate Similarity	NPD8072	Approved
0.7101	Intermediate Similarity	NPD7824	Approved
0.7098	Intermediate Similarity	NPD8073	Approved
0.7081	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7001	Phase 3
0.7074	Intermediate Similarity	NPD7470	Discontinued
0.7071	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8326	Phase 3
0.7069	Intermediate Similarity	NPD8325	Phase 3
0.7069	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD482	Approved
0.7051	Intermediate Similarity	NPD8431	Approved
0.704	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2509	Approved
0.7018	Intermediate Similarity	NPD2510	Approved
0.7017	Intermediate Similarity	NPD7730	Approved
0.7017	Intermediate Similarity	NPD7731	Approved
0.7012	Intermediate Similarity	NPD7789	Approved
0.7012	Intermediate Similarity	NPD7790	Approved
0.7012	Intermediate Similarity	NPD7950	Approved
0.7012	Intermediate Similarity	NPD7953	Approved
0.7012	Intermediate Similarity	NPD7951	Approved
0.7012	Intermediate Similarity	NPD7791	Approved
0.7012	Intermediate Similarity	NPD7952	Approved
0.7004	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2144	Approved
0.6977	Remote Similarity	NPD3038	Discontinued
0.6964	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7233	Approved
0.6941	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7234	Approved
0.6933	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7271	Approved
0.693	Remote Similarity	NPD6595	Phase 3
0.6926	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6999	Discontinued
0.6886	Remote Similarity	NPD6987	Phase 1
0.6886	Remote Similarity	NPD5901	Discontinued
0.6884	Remote Similarity	NPD4079	Approved
0.6884	Remote Similarity	NPD4076	Approved
0.688	Remote Similarity	NPD3389	Approved
0.688	Remote Similarity	NPD3394	Approved
0.688	Remote Similarity	NPD3393	Approved
0.6878	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5003	Discontinued
0.6867	Remote Similarity	NPD8094	Discontinued
0.6861	Remote Similarity	NPD7944	Discontinued
0.6858	Remote Similarity	NPD4501	Approved
0.6858	Remote Similarity	NPD4500	Approved
0.6854	Remote Similarity	NPD750	Phase 2
0.6851	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7780	Approved
0.6846	Remote Similarity	NPD7781	Approved
0.6837	Remote Similarity	NPD3506	Approved
0.6837	Remote Similarity	NPD3505	Approved
0.6826	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8093	Discontinued
0.6812	Remote Similarity	NPD8272	Phase 2
0.6812	Remote Similarity	NPD8282	Approved
0.6812	Remote Similarity	NPD8283	Approved
0.6812	Remote Similarity	NPD56	Approved
0.68	Remote Similarity	NPD7948	Phase 1
0.6797	Remote Similarity	NPD8423	Phase 2
0.6797	Remote Similarity	NPD8399	Phase 1
0.6786	Remote Similarity	NPD4427	Phase 2
0.6784	Remote Similarity	NPD484	Approved
0.677	Remote Similarity	NPD7777	Approved
0.677	Remote Similarity	NPD53	Approved
0.677	Remote Similarity	NPD7778	Approved
0.6769	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6242	Discontinued
0.6753	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8468	Phase 2
0.6727	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6664	Approved
0.6724	Remote Similarity	NPD7666	Phase 3
0.6724	Remote Similarity	NPD7665	Phase 2
0.6711	Remote Similarity	NPD7619	Phase 3
0.6711	Remote Similarity	NPD7618	Phase 3
0.6709	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6995	Phase 1
0.6705	Remote Similarity	NPD7708	Approved
0.6697	Remote Similarity	NPD5898	Approved
0.6697	Remote Similarity	NPD5897	Approved
0.6697	Remote Similarity	NPD5899	Approved
0.6697	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2565	Phase 2
0.6682	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2564	Approved
0.6682	Remote Similarity	NPD4499	Approved
0.6681	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7878	Phase 2
0.668	Remote Similarity	NPD3006	Discontinued
0.6667	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5065	Approved
0.6652	Remote Similarity	NPD7187	Phase 2
0.6652	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6635	Approved
0.6639	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD2844	Phase 3
0.6636	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6176	Phase 1
0.6603	Remote Similarity	NPD7803	Approved
0.6602	Remote Similarity	NPD7955	Approved
0.6602	Remote Similarity	NPD7956	Approved
0.6597	Remote Similarity	NPD5612	Discontinued
0.6595	Remote Similarity	NPD8098	Approved
0.6593	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1038	Approved
0.6575	Remote Similarity	NPD8386	Phase 2
0.6573	Remote Similarity	NPD8329	Phase 3
0.6571	Remote Similarity	NPD6026	Approved
0.6565	Remote Similarity	NPD6479	Discontinued
0.656	Remote Similarity	NPD4075	Phase 2
0.6558	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7711	Discontinued
0.6557	Remote Similarity	NPD7603	Discontinued
0.6552	Remote Similarity	NPD2920	Discontinued
0.6547	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8374	Phase 3
0.6542	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.654	Remote Similarity	NPD4852	Phase 2
0.6531	Remote Similarity	NPD6165	Phase 2
0.6531	Remote Similarity	NPD6164	Phase 2
0.6528	Remote Similarity	NPD1325	Approved
0.6528	Remote Similarity	NPD1326	Approved
0.6524	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3947	Discontinued
0.6523	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6523	Remote Similarity	NPD5482	Discontinued
0.6518	Remote Similarity	NPD7688	Phase 1
0.6513	Remote Similarity	NPD6531	Approved
0.6513	Remote Similarity	NPD6530	Approved
0.6508	Remote Similarity	NPD7576	Discontinued
0.6506	Remote Similarity	NPD8428	Approved
0.6506	Remote Similarity	NPD8427	Approved
0.6506	Remote Similarity	NPD8465	Approved
0.6506	Remote Similarity	NPD8467	Approved
0.6506	Remote Similarity	NPD8429	Approved
0.6506	Remote Similarity	NPD8466	Approved
0.649	Remote Similarity	NPD8289	Discontinued
0.6485	Remote Similarity	NPD7970	Approved
0.6485	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7941	Phase 3
0.6482	Remote Similarity	NPD8412	Phase 1
0.6481	Remote Similarity	NPD4640	Approved
0.6481	Remote Similarity	NPD4638	Approved
0.6481	Remote Similarity	NPD4639	Approved
0.6471	Remote Similarity	NPD8096	Phase 3
0.6471	Remote Similarity	NPD8097	Phase 3
0.6471	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8322	Phase 2
0.6466	Remote Similarity	NPD7558	Phase 2
0.6466	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD2172	Phase 1
0.6458	Remote Similarity	NPD8160	Phase 2
0.6456	Remote Similarity	NPD7465	Suspended
0.6455	Remote Similarity	NPD8123	Approved
0.6455	Remote Similarity	NPD4181	Approved
0.6455	Remote Similarity	NPD8122	Approved
0.6453	Remote Similarity	NPD8115	Approved
0.6453	Remote Similarity	NPD8114	Approved
0.645	Remote Similarity	NPD6249	Phase 2
0.645	Remote Similarity	NPD6248	Phase 2
0.6447	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD802	Phase 2
0.6444	Remote Similarity	NPD3961	Discontinued
0.6444	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7191	Phase 2
0.6431	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD8036	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data